I am actually open to all options, price points, and neighborhoods. Generally just looking for a place to begin my foodie research since I've heard so many good things about the dining scene in D.C. :)

Off the top of my head, my right now list for NYC would include: Red Barn, Parm, Miss Lilys, Don Antonio which I am trying tomorrow and Tertulia which I am trying on Sunday :)!

I had not heard of Boundary Stone and thought you meant Boundary Road. I then searched it and learned something new with great reviews... That being said, I'd add Boundary Road restaurant to your list...

With a two year old in tow, I'd avoid almost all the above, esp. Eve, Komi, Fiola, and Citronelle. Blue Duck Tavern will be fine. Check out Bibiana, Estadio, and Mintwood Place (all three are busy, lots of hustle and bustle, especially the latter two) and New Heights. Mintwood is a little less veg than the others. Rays the Steaks and Rays to the Third are kid friendly, and do have veg options, and there's 2Amys (extremely kid friendy) for that brunch you're thinking about (pizza and fresh doughnuts, that's brunch, right?) http://www.2amyspizza.com/ . Komi will do a veg menu, but getting reservations is really difficult, and limited to tables of four.

Totally different experiences. Obelisk is much smaller. More intimate setting and menu is entirely prix fixe. It's a fantastic meal -- allow 2 hours or so -- and I think it's the consistently best restaurant in the City (any cuisine). Dinner will be a series of great and interesting antipasti, a pasta course, and entree, cheese and dessert. Limited choices for the courses, but all consistently excellent with top notch ingrediaents and professional service. Fiola is bigger, more uneven, but more showy -- a bit more dinner as theater; more of a scene and more "see and be seen." Food at Fiola is good, and some is great, but it's much more inconsistent. Please don't take a two year old to Obelisk and think hard before taking a two year old to Fiola.

Expensive or "expensiv"er? Both are great, although Obelisk never thrills with their mains. Pasta is Fiola's forte IMO. Great cocktails at Fiola, quirky wines at Obelisk. Formal and elegant at Fiola, casual and more homey at Obelisk but with formal service. Noisier at Fiola.

I would go to Fiola, I think they are just doing amazing things right now, really well deserved James Beard nomination. And the staff are actually very nice and helpful. It's a great place. The pastas are great, really good duck preparation, great calamari and tartare appetizers, lots of good stuff.